Been trying to update the software on a 2014 Ram radio. After no success and calling the support line twice I was told the two thumb drives I tried weren't good ones for the transfer and to purchase a Kingston brand. What's your experience?

Had no issues on mine, don't remember the brand of drive but I don't think I have any Kingston thumbs. Kingston is a better drive, or at least was when I paid attention a few years ago.

The wife's Durango is getting "over the air" updates so no issues. My '13 Chrysler is supposed to be fussy about the flash drive I use for map updates, but my old 8 gig Verbatim works perfectly with it. I suspect dumb luck is responsible for my good fortune, other's have had a terrible time finding one to work well. FWIW, I've never updated the Uconnect proper, others who did it reported no noticeable effects from the updates.

Robert

The dealership upgraded mine for the most part when I got my oil changed there. There was one big update two years ago and they sent me a drive on a piece of cardboard to use. Can not imagine it was high grade but it did function as advertised. I think it was part of a recall.
Personally, I have used all brands but San Disk Cruiser is usually my go to for reliability and high speed transfers. If it works for streaming video, it will be fast enough for general data.
Craig